Omega-halogen-methyl-anthraquinone compound.



MAX HENRY ISLER, OF MANNHEIM, GERMANY, ASSIGNOR TO BADISOHE ANILIN &SODA FABRIK, OF LUDWIGSHAFEN-ON-THE-RHINE, GERMANY, A CORPORATION.

OME (BA-HALO GEN-3H3 THYL-ANTHRAQUIL'NONE COMPOUND fipecification ofLetters Patent.

Patented. July 14, 1908.

Application filed February 16, 1966. Serial No. 801,451.

tives which contain halogen in the side chain,

that is omega-halogen derivatives, and, according to the quantity ofhalogen employed, the substitution can be made to. take place to agreater, or lesser, extent.

My new halogen derivatives are characterized by being crystallinecompounds which are soluble in glacial acetic acid. They po'ssess awhite to yellow color and are very useful for the preparation ofcoloring matters.

The com ound which I wish to be understood as claiming specifically isomega-dichlOr-Z-methyl-anthra uinone which can be obtained in the-formof white crystals melting at a temperature of about two hundred ilegreescent1grade (200 C.) and which possesses a .composition corresponding tothe formula The following examples will serve to further illustrate thenature of my invention and how it may be carried into practical effeet,but my invention is not confined to these examples. The parts .are byweight.

'Example 1 Heat together, in an autoclave, for six (6) hours, at atemperature of one hundred and seventy (170) degrees centigrade, ten(10) parts of 2.- methyl anthra quinone and eight (8) parts of bromin,and treat the reaction product first with water and then extract it withalcohol in order to.

remove small quantities of impurities, and finally, if necessary,re-crystallize from glacial acetic acid. The compound produced melts ata temperature of about from two hundred (200) to two hundred and two(202) degrees centigrade, and-analysis points to its being a monobromderivative. The reaction can be carried out at a considerably lowertemperature, in which case, however, the time required to complete thereaction is much greater. if, in this example, double the quantity ofbromin be employed, and the reaction product be worked up in a similarmanner, the dibrom derivative is obtained.

Example 2. In order to obtain a chlorin derivative of 2 methylanthraquinone, treat this latter with chlorin at a temperature of fromone hundred and fifty (150) to one hundred and sixty (160) degreescentigrade. The mass melts after a short time. Continue passing inchlorin until the weight increases from about twenty (20) to twentyfive(25) per cent. In order to work up the reaction product, which consistsof a mixture of the monochlor and diehlor derivatives, powder and washwith water, and then treat with alcohol in which the monochlor derivative is easily soluble and from which it can be re-crystallized. Thepart which is difficultly soluble in alcohol can be re-crystallized fromglacial acetic acid and in this manner the dichlor derivative of 2-1nethly anthraquinone, melting at a temperature of two hundred (200)degrees centigrade, is obtained in the form of beautiful crystals.

Example 8. Heat together, in an autoclave, for six (6)-hours, at atemperature of one hundred and seventy (170) degrees centigrade, ten(10) parts of 2 methyl anthraquinone and twelve (12) parts of sulfuroxychlorid. Extract the reaction product by means of alcohol andcrystallize the residue from glacial acetic acid. The product soobtained is identical with the dichlor derivative of the foregoingExample 2. If, in this example, halt the quantity of sulfur oxychloridbe employed'the monoehlor derivative described in Example 2 is obtained.

Example. 4. Heat together, for six (6) hours, at a temperature of fromone hundred and sixty (160) to one hundred and seventy (170) degreescentigrade ten (10) parts of 1 chlor 2 methyl anthraquinone and seven(7) parts of bromin: Extract the reaction product by means of alcoholand crystallize the residue from glacial acetic acid.1-brom-2-methyl-anthraquinone reacts -in the same way if ten (10) artsthereof be heated with five and three-fifths (5.6)"parts of bromin.

Example 5. Heat together, for six '(6) hours, in an autoclave, atatemperature of from one hundred andsiirty (160) de rees centigrade, toone hundred and seventy 170) degrees centigrade, ten arts of l-chlor-2-methyl-anthraquinone an fourteen (14) parts of bromin and'work up thereaction product as described in the foregoing Exam- 7 ple 4.

Example 6. Heat together, for from four (4) to six (6) hours at atemperature of from one hundred and fifty (150) to one hundred andseventy (170) degrees centigrade, ten (10) parts of4-brom-1-liydroxy-2methylanthraquinone and .five (5) parts of bromin andcrystallize the reaction product from glacial acetic acid, whereupon thenew bromin derivative is obtained in the form of golden glitteringneedles. If, in this example, double the quantity of bromin be employed,the corresponding omega-dibrom derivative of bromhydroX'y-methyl-anthraquinone'is obtained. v p

Example 7. If the uantity oi halogen in the foregoing example beincreased and if,ior instance, ten (10) parts of methyl-anthraquinone betreated with twenty-four (24) parts of bromin the tribrom derivative ofinethyl-anthraquinonc can be, obtained. The reaction proceeds better ifa halogen carrier such for instance as iodin be present during. thereaction. monoand di-halogen derivatives in being very much morediiiicultly soluble in nearly all solvents.

Now what I claim is:

1. The process for the production of omega halogen derivatives of aZ-methyl-anthra: quinone body by acting on a Z-methyl-anstance.

This differs from the thraquinone body with a halogenizing sub 2. Therocess for-the production of omega halogen erivatives ofZ-methyl-anthraquinone by acting on Z-methyl-anthraquinonedichlor-2-methyl-anthraquinone which can' be obtained by acting on 2methyl-antliraquinone with chlorin and, which is a crystalline compoundand is soluble in glacial.

acetic acid, possesses a White color and melts at a temperature of abouttwo hundred degrees centigrade and which possesses a compositioncorresponding to the formula CHG12.

In testimony whereof I have hereunto set my hand in the presence of twosubscribing witne-isses. 1

MAX HENRY ISLER. Witnesses: I

J. Auto. LLOYD, Jos. H. Laura.

